(1-Adamant-yl)(4-amino-phen-yl)methanol.

In the racemic crystal of the title compound, C(17)H(23)NO, enanti-omers of the two crystallographically independent mol-ecules are linked into face-to-face RSdimers via inter-molecular O-H⋯N hydrogen bonds and π-π inter-actions with centroid-centroid distances of 3.7610 (2) Å. The mol-ecules adopt slightly different conformations and contain an adamantane cage consisting of three fused cyclo-hexane rings in almost ideal chair conformations, with C-C-C angles varying within the range 107.2 (4)-111.4 (4)°. In the hydrogen-bonded pair, the benzene rings are almost coplanar, the dihedral angle between them being 1.29 (13)°. The mol-ecular packing in the crystal is stabilized by additional inter-molecular N-H⋯O hydrogen bonds.

Related literature

The title compound was prepared according to a modification of the procedure of Adkins & Billica (1948 ▶). For some important properties of adamantane-bearing compounds, see: Cromwell et al. (1985 ▶), van Bommel et al. (2001 ▶).

Experimental

Crystal data

C17H23NO

M = 257.36

Monoclinic,

a = 8.8107 (5) Å

b = 12.1593 (6) Å

c = 26.6047 (16) Å

β = 93.046 (5)°

V = 2846.2 (3) Å3

Z = 8

Mo Kα radiation

μ = 0.07 mm−1

T = 120 K

0.40 × 0.40 × 0.10 mm

Data collection

Kuma KM-4 CCD diffractometer

Absorption correction: none

20748 measured reflections

5001 independent reflections

3444 reflections with I > 2σ(I)

R int = 0.039

Refinement

R[F 2 > 2σ(F 2)] = 0.094

wR(F 2) = 0.270

S = 1.19

5001 reflections

359 parameters

H atoms treated by a mixture of independent and constrained refinement

Δρmax = 0.49 e Å−3

Δρmin = −0.45 e Å−3

Data collection: CrysAlis CCD (Oxford Diffraction, 2006 ▶); cell refinement: CrysAlis CCD; data reduction: CrysAlis RED (Oxford Diffraction, 2006 ▶); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ▶); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008 ▶); molecular graphics: ORTEP-3 (Farrugia, 1997 ▶) and Mercury (Macrae et al., 2008 ▶); software used to prepare material for publication: SHELXL97.

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809012987/lh2796sup1.cif

Structure factors: contains datablocks I. DOI: 10.1107/S1600536809012987/lh2796Isup2.hkl

Additional supplementary materials: crystallographic information; 3D view; checkCIF report

C17H23NO	F(000) = 1120
Mr = 257.36	Dx = 1.201 Mg m−3
Monoclinic, P21/n	Melting point: 145 K
Hall symbol: -P 2yn	Mo Kα radiation, λ = 0.71073 Å
a = 8.8107 (5) Å	Cell parameters from 5001 reflections
b = 12.1593 (6) Å	θ = 2.9–25.0°
c = 26.6047 (16) Å	µ = 0.07 mm−1
β = 93.046 (5)°	T = 120 K
V = 2846.2 (3) Å3	Block, white
Z = 8	0.40 × 0.40 × 0.10 mm

Kuma KM-4 CCD diffractometer	3444 reflections with I > 2σ(I)
Radiation source: fine-focus sealed tube	Rint = 0.039
graphite	θmax = 25.0°, θmin = 2.9°
Detector resolution: 0.06 pixels mm-1	h = −10→9
ω scans	k = −13→14
20748 measured reflections	l = −30→31
5001 independent reflections

Refinement on F2	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F2 > 2σ(F2)] = 0.094	Hydrogen site location: inferred from neighbouring sites
wR(F2) = 0.270	H atoms treated by a mixture of independent and constrained refinement
S = 1.19	w = 1/[σ2(Fo2) + (0.0778P)2 + 11.8176P] where P = (Fo2 + 2Fc2)/3
5001 reflections	(Δ/σ)max < 0.001
359 parameters	Δρmax = 0.49 e Å−3
0 restraints	Δρmin = −0.45 e Å−3

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F2 against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The threshold expression of F2 > 2σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

	x	y	z	Uiso*/Ueq
O2	0.2678 (3)	0.0244 (2)	0.16941 (11)	0.0232 (7)
H2A	0.1904	0.0043	0.1841	0.035*
O1	−0.2643 (3)	0.3748 (2)	0.32906 (12)	0.0237 (7)
H1A	−0.1885	0.3958	0.3138	0.036*
N2	−0.0279 (4)	0.4483 (3)	0.26652 (16)	0.0233 (9)
N1	0.0312 (4)	−0.0498 (3)	0.23253 (16)	0.0212 (8)
C31	0.2335 (5)	0.1227 (4)	0.14084 (16)	0.0204 (9)
H31A	0.1542	0.1032	0.1140	0.025*
C36	0.1502 (4)	0.2991 (3)	0.25476 (16)	0.0173 (9)
H36A	0.1831	0.3043	0.2893	0.021*
C11	−0.2249 (4)	0.2800 (4)	0.35820 (16)	0.0188 (9)
H11A	−0.1447	0.3016	0.3843	0.023*
C37	0.2122 (4)	0.2203 (3)	0.22438 (16)	0.0166 (9)
H37A	0.2875	0.1718	0.2385	0.020*
C15	−0.0345 (4)	0.0279 (3)	0.26470 (16)	0.0176 (9)
C17	−0.2079 (5)	0.1796 (4)	0.27497 (16)	0.0208 (9)
H17A	−0.2848	0.2270	0.2610	0.025*
C35	0.0382 (5)	0.3716 (3)	0.23442 (16)	0.0196 (9)
C16	−0.1464 (4)	0.0999 (4)	0.24464 (16)	0.0195 (9)
H16A	−0.1803	0.0941	0.2102	0.023*
C34	−0.0086 (5)	0.3614 (4)	0.18438 (17)	0.0221 (10)
H34A	−0.0841	0.4097	0.1702	0.026*
C14	0.0149 (5)	0.0395 (4)	0.31485 (17)	0.0216 (10)
H14A	0.0908	−0.0085	0.3290	0.026*
C13	−0.0459 (4)	0.1208 (4)	0.34459 (17)	0.0217 (10)
H13A	−0.0092	0.1282	0.3787	0.026*
C32	0.1667 (4)	0.2106 (3)	0.17363 (16)	0.0171 (9)
C33	0.0537 (5)	0.2811 (4)	0.15445 (17)	0.0201 (9)
H33A	0.0184	0.2744	0.1202	0.024*
C21	0.3783 (5)	0.1564 (3)	0.11427 (16)	0.0189 (9)
C12	−0.1594 (5)	0.1918 (4)	0.32555 (16)	0.0193 (9)
C30	0.4344 (5)	0.0582 (4)	0.08343 (18)	0.0247 (10)
H30A	0.4603	−0.0041	0.1063	0.030*
H30B	0.3522	0.0339	0.0591	0.030*
C8	−0.4950 (5)	0.2002 (4)	0.34928 (16)	0.0211 (10)
H8A	−0.4571	0.1361	0.3307	0.025*
H8B	−0.5245	0.2581	0.3245	0.025*
C6	−0.6949 (5)	0.2663 (4)	0.40555 (18)	0.0285 (11)
H6A	−0.7243	0.3243	0.3808	0.034*
H6B	−0.7860	0.2458	0.4237	0.034*
C28	0.5085 (5)	0.1941 (4)	0.15176 (16)	0.0196 (9)
H28A	0.4754	0.2592	0.1707	0.023*
H28B	0.5331	0.1345	0.1762	0.023*
C27	0.6498 (5)	0.2230 (4)	0.12352 (16)	0.0213 (9)
H27A	0.7332	0.2453	0.1484	0.026*
C1	−0.3687 (4)	0.2436 (4)	0.38585 (16)	0.0200 (9)
C26	0.7028 (5)	0.1259 (4)	0.09309 (17)	0.0248 (10)
H26A	0.7301	0.0638	0.1159	0.030*
H26B	0.7943	0.1468	0.0752	0.030*
C7	−0.6353 (5)	0.1658 (4)	0.37817 (18)	0.0289 (11)
H7A	−0.7164	0.1371	0.3539	0.035*
C5	−0.5715 (5)	0.3100 (4)	0.44299 (18)	0.0292 (11)
H5A	−0.6109	0.3755	0.4610	0.035*
C10	−0.4314 (5)	0.3433 (4)	0.41430 (18)	0.0286 (11)
H10A	−0.3515	0.3721	0.4384	0.034*
H10B	−0.4596	0.4025	0.3900	0.034*
C22	0.3428 (5)	0.2528 (4)	0.07819 (18)	0.0282 (11)
H22A	0.3084	0.3167	0.0976	0.034*
H22B	0.2592	0.2316	0.0538	0.034*
C25	0.5754 (5)	0.0907 (4)	0.05480 (18)	0.0307 (11)
H25A	0.6099	0.0264	0.0350	0.037*
C29	0.6129 (5)	0.3197 (4)	0.08773 (19)	0.0307 (11)
H29A	0.7044	0.3401	0.0698	0.037*
H29B	0.5811	0.3843	0.1072	0.037*
C23	0.4837 (5)	0.2858 (4)	0.04936 (18)	0.0313 (12)
H23A	0.4578	0.3485	0.0262	0.038*
C24	0.5362 (6)	0.1869 (5)	0.01922 (18)	0.0340 (12)
H24A	0.6266	0.2073	0.0008	0.041*
H24B	0.4545	0.1646	−0.0057	0.041*
C4	−0.5269 (6)	0.2204 (5)	0.48089 (19)	0.0420 (14)
H4A	−0.6164	0.1985	0.4995	0.050*
H4B	−0.4479	0.2485	0.5055	0.050*
C2	−0.3263 (5)	0.1538 (4)	0.42432 (19)	0.0335 (12)
H2D	−0.2448	0.1809	0.4482	0.040*
H2E	−0.2874	0.0886	0.4068	0.040*
C9	−0.5907 (6)	0.0769 (4)	0.4164 (2)	0.0424 (14)
H9A	−0.5532	0.0112	0.3989	0.051*
H9B	−0.6804	0.0550	0.4350	0.051*
C3	−0.4660 (6)	0.1212 (5)	0.4533 (2)	0.0456 (15)
H3A	−0.4363	0.0626	0.4784	0.055*
H1C	0.078 (5)	−0.107 (4)	0.2492 (17)	0.017 (11)*
H2C	−0.081 (7)	0.496 (5)	0.248 (2)	0.043 (17)*
H1B	−0.029 (6)	−0.075 (5)	0.211 (2)	0.033 (15)*
H2B	0.039 (7)	0.482 (5)	0.289 (2)	0.057 (19)*

	U11	U22	U33	U12	U13	U23
O2	0.0184 (15)	0.0165 (16)	0.0354 (18)	0.0006 (12)	0.0083 (13)	0.0024 (13)
O1	0.0180 (15)	0.0158 (16)	0.0380 (18)	−0.0019 (12)	0.0085 (13)	0.0016 (13)
N2	0.0170 (19)	0.021 (2)	0.032 (2)	0.0003 (17)	0.0049 (17)	−0.0027 (18)
N1	0.0172 (19)	0.0143 (19)	0.032 (2)	0.0021 (16)	0.0040 (17)	−0.0019 (17)
C31	0.016 (2)	0.017 (2)	0.028 (2)	−0.0029 (17)	−0.0001 (17)	−0.0032 (18)
C36	0.0102 (19)	0.018 (2)	0.024 (2)	−0.0028 (16)	0.0021 (16)	0.0008 (17)
C11	0.0104 (19)	0.021 (2)	0.026 (2)	0.0003 (17)	0.0028 (16)	0.0023 (18)
C37	0.0107 (18)	0.012 (2)	0.027 (2)	−0.0021 (16)	0.0017 (16)	0.0017 (17)
C15	0.0091 (18)	0.017 (2)	0.027 (2)	−0.0040 (16)	0.0053 (16)	−0.0003 (17)
C17	0.0119 (19)	0.024 (2)	0.027 (2)	−0.0005 (17)	0.0023 (17)	0.0032 (19)
C35	0.016 (2)	0.014 (2)	0.029 (2)	−0.0037 (17)	0.0067 (17)	−0.0005 (18)
C16	0.015 (2)	0.019 (2)	0.025 (2)	−0.0030 (17)	0.0017 (17)	0.0002 (18)
C34	0.013 (2)	0.019 (2)	0.034 (3)	−0.0019 (17)	0.0007 (18)	0.0048 (19)
C14	0.0119 (19)	0.018 (2)	0.034 (3)	0.0002 (17)	0.0010 (17)	0.0039 (19)
C13	0.013 (2)	0.026 (2)	0.026 (2)	−0.0018 (18)	−0.0001 (17)	0.0014 (19)
C32	0.0097 (19)	0.015 (2)	0.027 (2)	−0.0025 (16)	0.0037 (16)	0.0008 (17)
C33	0.014 (2)	0.021 (2)	0.026 (2)	−0.0025 (17)	−0.0001 (17)	0.0016 (18)
C21	0.016 (2)	0.019 (2)	0.022 (2)	0.0009 (17)	0.0018 (17)	−0.0020 (18)
C12	0.014 (2)	0.021 (2)	0.023 (2)	−0.0050 (17)	0.0044 (17)	0.0010 (18)
C30	0.023 (2)	0.020 (2)	0.031 (3)	−0.0003 (19)	0.0063 (19)	−0.0067 (19)
C8	0.017 (2)	0.022 (2)	0.025 (2)	−0.0054 (18)	0.0045 (18)	−0.0031 (18)
C6	0.013 (2)	0.042 (3)	0.030 (3)	−0.006 (2)	0.0062 (18)	0.000 (2)
C28	0.016 (2)	0.022 (2)	0.021 (2)	−0.0045 (17)	0.0029 (17)	0.0001 (18)
C27	0.019 (2)	0.022 (2)	0.024 (2)	−0.0066 (18)	0.0048 (17)	−0.0020 (18)
C1	0.0121 (19)	0.025 (2)	0.023 (2)	−0.0019 (18)	0.0014 (16)	0.0013 (19)
C26	0.020 (2)	0.023 (2)	0.032 (3)	0.0020 (18)	0.0071 (18)	−0.001 (2)
C7	0.022 (2)	0.032 (3)	0.033 (3)	−0.010 (2)	0.006 (2)	−0.005 (2)
C5	0.021 (2)	0.036 (3)	0.032 (3)	−0.005 (2)	0.0091 (19)	−0.013 (2)
C10	0.018 (2)	0.038 (3)	0.030 (3)	−0.006 (2)	0.0040 (19)	−0.010 (2)
C22	0.022 (2)	0.034 (3)	0.029 (2)	0.006 (2)	0.0035 (19)	0.009 (2)
C25	0.030 (3)	0.032 (3)	0.031 (3)	−0.003 (2)	0.008 (2)	−0.006 (2)
C29	0.031 (3)	0.020 (2)	0.043 (3)	−0.007 (2)	0.018 (2)	0.001 (2)
C23	0.031 (3)	0.037 (3)	0.027 (3)	0.003 (2)	0.010 (2)	0.012 (2)
C24	0.030 (3)	0.051 (3)	0.021 (2)	−0.002 (2)	0.007 (2)	0.001 (2)
C4	0.024 (3)	0.077 (4)	0.025 (3)	0.000 (3)	0.006 (2)	0.001 (3)
C2	0.028 (3)	0.041 (3)	0.032 (3)	0.012 (2)	0.007 (2)	0.014 (2)
C9	0.041 (3)	0.027 (3)	0.062 (4)	0.000 (2)	0.030 (3)	0.009 (3)
C3	0.036 (3)	0.056 (4)	0.046 (3)	0.008 (3)	0.012 (2)	0.023 (3)

O2—C31	1.440 (5)	C8—H8B	0.9900
O2—H2A	0.8400	C6—C5	1.530 (6)
O1—C11	1.422 (5)	C6—C7	1.530 (7)
O1—H1A	0.8400	C6—H6A	0.9900
N2—C35	1.411 (6)	C6—H6B	0.9900
N2—H2C	0.88 (6)	C28—C27	1.529 (6)
N2—H2B	0.91 (7)	C28—H28A	0.9900
N1—C15	1.419 (5)	C28—H28B	0.9900
N1—H1C	0.91 (5)	C27—C26	1.519 (6)
N1—H1B	0.83 (6)	C27—C29	1.537 (6)
C31—C32	1.518 (6)	C27—H27A	1.0000
C31—C21	1.547 (6)	C1—C2	1.529 (6)
C31—H31A	1.0000	C1—C10	1.547 (6)
C36—C37	1.384 (6)	C26—C25	1.537 (6)
C36—C35	1.410 (6)	C26—H26A	0.9900
C36—H36A	0.9500	C26—H26B	0.9900
C11—C12	1.514 (6)	C7—C9	1.522 (7)
C11—C1	1.562 (6)	C7—H7A	1.0000
C11—H11A	1.0000	C5—C4	1.523 (8)
C37—C32	1.393 (6)	C5—C10	1.540 (6)
C37—H37A	0.9500	C5—H5A	1.0000
C15—C14	1.389 (6)	C10—H10A	0.9900
C15—C16	1.402 (6)	C10—H10B	0.9900
C17—C16	1.390 (6)	C22—C23	1.546 (6)
C17—C12	1.398 (6)	C22—H22A	0.9900
C17—H17A	0.9500	C22—H22B	0.9900
C35—C34	1.378 (6)	C25—C24	1.533 (7)
C16—H16A	0.9500	C25—H25A	1.0000
C34—C33	1.391 (6)	C29—C23	1.544 (7)
C34—H34A	0.9500	C29—H29A	0.9900
C14—C13	1.390 (6)	C29—H29B	0.9900
C14—H14A	0.9500	C23—C24	1.530 (7)
C13—C12	1.396 (6)	C23—H23A	1.0000
C13—H13A	0.9500	C24—H24A	0.9900
C32—C33	1.391 (6)	C24—H24B	0.9900
C33—H33A	0.9500	C4—C3	1.524 (8)
C21—C22	1.536 (6)	C4—H4A	0.9900
C21—C30	1.545 (6)	C4—H4B	0.9900
C21—C28	1.549 (6)	C2—C3	1.539 (7)
C30—C25	1.543 (6)	C2—H2D	0.9900
C30—H30A	0.9900	C2—H2E	0.9900
C30—H30B	0.9900	C9—C3	1.533 (8)
C8—C1	1.532 (6)	C9—H9A	0.9900
C8—C7	1.548 (6)	C9—H9B	0.9900
C8—H8A	0.9900	C3—H3A	1.0000
C31—O2—H2A	109.5	C28—C27—C29	109.2 (4)
C11—O1—H1A	109.5	C26—C27—H27A	109.1
C35—N2—H2C	109 (4)	C28—C27—H27A	109.1
C35—N2—H2B	115 (4)	C29—C27—H27A	109.1
H2C—N2—H2B	112 (6)	C2—C1—C8	108.8 (4)
C15—N1—H1C	114 (3)	C2—C1—C10	108.2 (4)
C15—N1—H1B	114 (4)	C8—C1—C10	108.3 (3)
H1C—N1—H1B	109 (5)	C2—C1—C11	110.0 (3)
O2—C31—C32	111.0 (3)	C8—C1—C11	112.2 (3)
O2—C31—C21	107.8 (3)	C10—C1—C11	109.1 (4)
C32—C31—C21	115.5 (3)	C27—C26—C25	109.6 (4)
O2—C31—H31A	107.4	C27—C26—H26A	109.8
C32—C31—H31A	107.4	C25—C26—H26A	109.8
C21—C31—H31A	107.4	C27—C26—H26B	109.8
C37—C36—C35	119.9 (4)	C25—C26—H26B	109.8
C37—C36—H36A	120.0	H26A—C26—H26B	108.2
C35—C36—H36A	120.0	C9—C7—C6	109.4 (4)
O1—C11—C12	110.5 (3)	C9—C7—C8	109.8 (4)
O1—C11—C1	107.8 (3)	C6—C7—C8	108.9 (4)
C12—C11—C1	114.4 (4)	C9—C7—H7A	109.6
O1—C11—H11A	108.0	C6—C7—H7A	109.6
C12—C11—H11A	108.0	C8—C7—H7A	109.6
C1—C11—H11A	108.0	C4—C5—C6	109.4 (4)
C36—C37—C32	121.5 (4)	C4—C5—C10	109.3 (4)
C36—C37—H37A	119.3	C6—C5—C10	109.2 (4)
C32—C37—H37A	119.3	C4—C5—H5A	109.6
C14—C15—C16	118.7 (4)	C6—C5—H5A	109.6
C14—C15—N1	122.0 (4)	C10—C5—H5A	109.6
C16—C15—N1	119.2 (4)	C5—C10—C1	110.7 (4)
C16—C17—C12	121.6 (4)	C5—C10—H10A	109.5
C16—C17—H17A	119.2	C1—C10—H10A	109.5
C12—C17—H17A	119.2	C5—C10—H10B	109.5
C34—C35—C36	118.8 (4)	C1—C10—H10B	109.5
C34—C35—N2	122.1 (4)	H10A—C10—H10B	108.1
C36—C35—N2	119.0 (4)	C21—C22—C23	111.4 (4)
C17—C16—C15	120.1 (4)	C21—C22—H22A	109.3
C17—C16—H16A	119.9	C23—C22—H22A	109.3
C15—C16—H16A	119.9	C21—C22—H22B	109.3
C35—C34—C33	120.6 (4)	C23—C22—H22B	109.3
C35—C34—H34A	119.7	H22A—C22—H22B	108.0
C33—C34—H34A	119.7	C24—C25—C26	109.2 (4)
C15—C14—C13	120.6 (4)	C24—C25—C30	109.9 (4)
C15—C14—H14A	119.7	C26—C25—C30	108.9 (4)
C13—C14—H14A	119.7	C24—C25—H25A	109.6
C14—C13—C12	121.5 (4)	C26—C25—H25A	109.6
C14—C13—H13A	119.2	C30—C25—H25A	109.6
C12—C13—H13A	119.2	C27—C29—C23	109.2 (4)
C33—C32—C37	117.8 (4)	C27—C29—H29A	109.8
C33—C32—C31	121.0 (4)	C23—C29—H29A	109.8
C37—C32—C31	121.1 (4)	C27—C29—H29B	109.8
C32—C33—C34	121.3 (4)	C23—C29—H29B	109.8
C32—C33—H33A	119.4	H29A—C29—H29B	108.3
C34—C33—H33A	119.4	C24—C23—C29	108.9 (4)
C22—C21—C30	108.6 (4)	C24—C23—C22	109.2 (4)
C22—C21—C31	110.0 (3)	C29—C23—C22	108.9 (4)
C30—C21—C31	109.4 (3)	C24—C23—H23A	109.9
C22—C21—C28	107.2 (4)	C29—C23—H23A	109.9
C30—C21—C28	108.9 (3)	C22—C23—H23A	109.9
C31—C21—C28	112.6 (3)	C23—C24—C25	109.9 (4)
C13—C12—C17	117.4 (4)	C23—C24—H24A	109.7
C13—C12—C11	121.2 (4)	C25—C24—H24A	109.7
C17—C12—C11	121.4 (4)	C23—C24—H24B	109.7
C25—C30—C21	110.6 (4)	C25—C24—H24B	109.7
C25—C30—H30A	109.5	H24A—C24—H24B	108.2
C21—C30—H30A	109.5	C5—C4—C3	109.5 (4)
C25—C30—H30B	109.5	C5—C4—H4A	109.8
C21—C30—H30B	109.5	C3—C4—H4A	109.8
H30A—C30—H30B	108.1	C5—C4—H4B	109.8
C1—C8—C7	110.5 (4)	C3—C4—H4B	109.8
C1—C8—H8A	109.6	H4A—C4—H4B	108.2
C7—C8—H8A	109.6	C1—C2—C3	110.2 (4)
C1—C8—H8B	109.6	C1—C2—H2D	109.6
C7—C8—H8B	109.6	C3—C2—H2D	109.6
H8A—C8—H8B	108.1	C1—C2—H2E	109.6
C5—C6—C7	109.8 (4)	C3—C2—H2E	109.6
C5—C6—H6A	109.7	H2D—C2—H2E	108.1
C7—C6—H6A	109.7	C7—C9—C3	109.3 (4)
C5—C6—H6B	109.7	C7—C9—H9A	109.8
C7—C6—H6B	109.7	C3—C9—H9A	109.8
H6A—C6—H6B	108.2	C7—C9—H9B	109.8
C27—C28—C21	110.2 (3)	C3—C9—H9B	109.8
C27—C28—H28A	109.6	H9A—C9—H9B	108.3
C21—C28—H28A	109.6	C4—C3—C9	109.1 (4)
C27—C28—H28B	109.6	C4—C3—C2	110.4 (5)
C21—C28—H28B	109.6	C9—C3—C2	109.5 (4)
H28A—C28—H28B	108.1	C4—C3—H3A	109.2
C26—C27—C28	111.4 (4)	C9—C3—H3A	109.2
C26—C27—C29	109.0 (4)	C2—C3—H3A	109.2

D—H···A	D—H	H···A	D···A	D—H···A
O2—H2A···N1	0.84	2.06	2.890 (5)	168
O1—H1A···N2	0.84	2.04	2.876 (5)	171
N1—H1B···O1i	0.83 (6)	2.15 (6)	2.941 (5)	162 (5)
N2—H2B···O2ii	0.91 (7)	2.05 (7)	2.932 (5)	163 (6)

Table 1

Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
O2—H2A⋯N1	0.84	2.06	2.890 (5)	168
O1—H1A⋯N2	0.84	2.04	2.876 (5)	171
N1—H1B⋯O1i	0.83 (6)	2.15 (6)	2.941 (5)	162 (5)
N2—H2B⋯O2ii	0.91 (7)	2.05 (7)	2.932 (5)	163 (6)

Symmetry codes: (i) ; (ii) .